Kick off your Holiday shopping season in style! This year’s Shop + Stroll event will feature a stylish line-up of independently owned shops, boutiques, pop-ups, food, drink and entertaining festivities that will kick off your holiday season in style! Get ready to shop, stroll, sip and snack as you enjoy exclusive holiday cheer in Winchester Center’s Historic District. A live drawing for a winner in the Red Ticket Raffle of $1,000 and $500 will take place at 9 pm at Leading Edge Real Estate!